EP0496237A3 - N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohept(b)indole - Google Patents

N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohept(b)indole Download PDF

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Publication number
EP0496237A3
EP0496237A3 EP19920100414 EP92100414A EP0496237A3 EP 0496237 A3 EP0496237 A3 EP 0496237A3 EP 19920100414 EP19920100414 EP 19920100414 EP 92100414 A EP92100414 A EP 92100414A EP 0496237 A3 EP0496237 A3 EP 0496237A3
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EP
European Patent Office
Prior art keywords
branched
alkyl
hydrogen
straight
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP19920100414
Other versions
EP0496237B1 (en
EP0496237A2 (en
Inventor
Paolo Cozzi
Antonio Pillan
Maurizio Pulici
Patricia Salvati
Angelo Daniele Volpi
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Pfizer Italia SRL
Original Assignee
Farmitalia Carlo Erba SRL
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Application filed by Farmitalia Carlo Erba SRL filed Critical Farmitalia Carlo Erba SRL
Publication of EP0496237A2 publication Critical patent/EP0496237A2/en
Publication of EP0496237A3 publication Critical patent/EP0496237A3/en
Application granted granted Critical
Publication of EP0496237B1 publication Critical patent/EP0496237B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Reproductive Health (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention provides new N-imidazolyl derivatives of substituted tetrahydrocarbazoles and cyclopent[b]indoles of general formula (I) <CHEM> wherein n is 1 or 2; p is an integer of 1 to 4; A is a straight or branched C1-C4 alkylene chain; B is a direct linkage, a straight or branched, unsaturated or saturated C1-C4 alkylene chain; Q is a direct linkage or a straight or branched C1-C4 alkylene chain; each of R1 and R2 independently is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, halogen or trihalomethyl; each of R3 and R5, independently is hydrogen or C1-C4 alkyl; R4 is -OR6 or -N(R6,R7) group, wherein each of R6 and R7 independently is hydrogen, C1-C4 alkyl, phenyl or benzyl; or a pharmaceutically acceptable salt thereof, which are useful in the treatment of a disease state in which an enhancement of TxA2 synthesis exerts a pathogenic effect.
EP92100414A 1991-01-22 1992-01-13 N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohept[b]indole Expired - Lifetime EP0496237B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9101375 1991-01-22
GB919101375A GB9101375D0 (en) 1991-01-22 1991-01-22 N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohepht(b)indole

Publications (3)

Publication Number Publication Date
EP0496237A2 EP0496237A2 (en) 1992-07-29
EP0496237A3 true EP0496237A3 (en) 1992-12-09
EP0496237B1 EP0496237B1 (en) 1996-02-14

Family

ID=10688812

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92100414A Expired - Lifetime EP0496237B1 (en) 1991-01-22 1992-01-13 N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohept[b]indole

Country Status (18)

Country Link
US (1) US5238953A (en)
EP (1) EP0496237B1 (en)
JP (1) JPH04321683A (en)
KR (1) KR920014806A (en)
AT (1) ATE134191T1 (en)
AU (1) AU641837B2 (en)
CA (1) CA2059741A1 (en)
DE (1) DE69208271D1 (en)
FI (1) FI920247A (en)
GB (1) GB9101375D0 (en)
HU (1) HUT60492A (en)
IE (1) IE920173A1 (en)
IL (1) IL100646A (en)
MX (1) MX9200178A (en)
MY (1) MY106807A (en)
NZ (1) NZ241317A (en)
TW (1) TW203610B (en)
ZA (1) ZA92428B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1050840C (en) * 1993-06-14 2000-03-29 美国辉瑞有限公司 Imidazole lipoxygenase inhibitors
DE4435477A1 (en) 1994-10-04 1996-04-11 Bayer Ag Cycloalkano-indole and -azaindole derivatives
US6177440B1 (en) 1996-10-30 2001-01-23 Eli Lilly And Company Substituted tricyclics
US6713645B1 (en) * 1996-10-30 2004-03-30 Eli Lilly And Company Substituted tricyclics
US6410583B1 (en) 2000-07-25 2002-06-25 Merck Frosst Canada & Co. Cyclopentanoindoles, compositions containing such compounds and methods of treatment
AR038136A1 (en) 2002-01-24 2004-12-29 Merck Frosst Canada Inc CYCLALCANINDOLS WITH REPLACEMENT WITH FLUOR COMPOSITIONS CONTAINING THESE COMPOUNDS AND TREATMENT METHODS

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR976484A (en) * 1947-12-24 1951-03-19 Ciba Geigy Process for the preparation of new imidazolines
US3970757A (en) * 1973-06-02 1976-07-20 Pfizer Inc. Tetrahydro-carbazole derivatives as gastric anti-secretory agents
EP0073663A2 (en) * 1981-08-26 1983-03-09 Pfizer Limited Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
EP0107618A1 (en) * 1982-09-30 1984-05-02 Ciba-Geigy Ag N-substituted-2-(1-imidazolyl)-indoles
EP0234708A1 (en) * 1986-01-23 1987-09-02 Merck Frosst Canada Inc. Tetrahydrocarbazole 1-alkanoic acids
EP0310179A2 (en) * 1987-09-28 1989-04-05 Merck Frosst Canada Inc. Tetrahydrocarbazole esters
EP0363789A1 (en) * 1988-10-06 1990-04-18 FARMITALIA CARLO ERBA S.r.l. N-imidazolyl-and N-imidazolyl-methyl derivatives or substituted bicyclic compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1046519A (en) * 1975-08-28 1979-01-16 American Home Products Corporation Trycyclic acetic acid derivatives
US4808608A (en) * 1986-01-23 1989-02-28 Merck & Co., Inc. Tetrahydrocarbazole 1-alkanoic acids, pharmaceutical compositions and use
CA1326030C (en) * 1987-07-21 1994-01-11 John W. Gillard Cyclohept[b]indolealkanoic acids
DK185489A (en) * 1988-04-22 1989-10-23 Duphar Int Res IMIDAZOLYLMETHYL-CYCLOALKANOEBAA INDOLONES, THEIR PREPARATION AND USE
US5187180A (en) * 1990-07-26 1993-02-16 Merck Frosst Canada, Inc. (quinolin-2-ylmethoxy)heterotetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes
US5221678A (en) * 1990-07-26 1993-06-22 Merck Frosst Canada, Inc. (quinolin-2-ylmethoxy)tetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR976484A (en) * 1947-12-24 1951-03-19 Ciba Geigy Process for the preparation of new imidazolines
US3970757A (en) * 1973-06-02 1976-07-20 Pfizer Inc. Tetrahydro-carbazole derivatives as gastric anti-secretory agents
EP0073663A2 (en) * 1981-08-26 1983-03-09 Pfizer Limited Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
EP0107618A1 (en) * 1982-09-30 1984-05-02 Ciba-Geigy Ag N-substituted-2-(1-imidazolyl)-indoles
EP0234708A1 (en) * 1986-01-23 1987-09-02 Merck Frosst Canada Inc. Tetrahydrocarbazole 1-alkanoic acids
EP0310179A2 (en) * 1987-09-28 1989-04-05 Merck Frosst Canada Inc. Tetrahydrocarbazole esters
EP0363789A1 (en) * 1988-10-06 1990-04-18 FARMITALIA CARLO ERBA S.r.l. N-imidazolyl-and N-imidazolyl-methyl derivatives or substituted bicyclic compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ANNU. REP. MED. CHEM vol. 22, 1987, pages 95 - 105 *
ANNU. REP. MED. CHEM. vol. 25, 1990, pages 99 - 108 *

Also Published As

Publication number Publication date
NZ241317A (en) 1993-08-26
ZA92428B (en) 1992-10-28
AU1020792A (en) 1992-07-30
IL100646A (en) 1995-11-27
HU9200190D0 (en) 1992-04-28
ATE134191T1 (en) 1996-02-15
MX9200178A (en) 1992-07-01
FI920247A (en) 1992-07-23
US5238953A (en) 1993-08-24
AU641837B2 (en) 1993-09-30
IL100646A0 (en) 1992-09-06
DE69208271D1 (en) 1996-03-28
HUT60492A (en) 1992-09-28
JPH04321683A (en) 1992-11-11
EP0496237B1 (en) 1996-02-14
MY106807A (en) 1995-07-31
TW203610B (en) 1993-04-11
KR920014806A (en) 1992-08-25
CA2059741A1 (en) 1992-07-23
GB9101375D0 (en) 1991-03-06
EP0496237A2 (en) 1992-07-29
IE920173A1 (en) 1992-07-29
FI920247A0 (en) 1992-01-20

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